HCID 71152421, compound → HCID 89315743, compound

Participants

Reaction Steps

To a solution of (3 aS,4R,5R,6R,7aS)-6-(hydroxymethyl)-2-oxooctahydrobenzo[d]oxazole-4,5-diyl dibenzoate (1.76 g, 4.28 mmol) in dry DCM (40 mL) at 0° C. was added DMP (2.72 g, 6.42 mmol). The mixture was then stirred at room temperature for 4 h. The reaction was diluted with saturated aqueous NaHCO3 (20 mL) and 1 M Na2S2O3 (30 mL) and extracted with EtOAc (2×50 mL). The extracts were dried over MgSO4 and the solvents were evaporated to give (3aS,4R,5R,6S,7aS)-6-formyl-2-oxooctahydrobenzo[d]oxazole-4,5-diyl dibenzoate (1.75 g, 100%) which was carried onto next reaction without further purification. 1H NMR (400 MHz, CDCl3) δ 9.82 (s, 1H), 7.95 (d, J=7.8 Hz, 2H), 7.88 (d, J=7.8 Hz, 2H), 7.47-7.54 (m, 2H), 7.32-7.38 (m, 4H), 6.48 (s, 1H), 5.66 (t, J=8.2 Hz, 1H), 5.50 (dd, J=7.7 Hz, 5.8 Hz, 1H), 4.94-4.97 (m, 1H), 4.00 (t, J=6.6 Hz, 1H), 3.26-3.32 (m, 1H), 2.56 (dt, J=12.1 Hz, 2.5 Hz, 1H), 2.10-2.18 (m, 1H).

Provenance & Evidence